How do get Apple Card and Quicken to enable the automatic transaction between them? What is that process? No workarounds please.

Not all card issuers link through Quicken. An increasing number of my cards no longer allow web connection (either due to costs, security concerns, or something else). You can download your monthly transactions after a statement has been generated.

Connecting to Quicken is not “ basic functionality” by any means. The card issuer chooses whether or not to support Quicken Connect and Goldman Sachs Bank (the issuer of the Apple Card) has chosen to not support it for whatever reason. Calls to Goldman Sachs Bank about it have resulted in stonewalling. The only other credit card Goldman Sachs Bank issues is the GM Mastercard and it also does not support Quicken Connect. Quicken community forums have been lit up about this since the release of the Apple Card but unless the bank chooses to support the feature there’s nothing Quicken can do about it.

One of AppleCard’s PRIMARY selling points was / is privacy and security.

It requires Apple “Trusted Devices,” 2FA, and Biometric-based authentication to see your account in “real time.”

Allowing Quicken - and their sub-contractors - real-time access to your account is essentially opposite to Apple’s security construct.

Air-gapped, monthly, batch-processed downloads are likely the best we’re going to get for the foreseeable future.

I too was once a “Heavy” Quicken “live connect” user for maybe 15+ years … until I researched into “how the sausage was actually made” … and “pulled the plug” on ALL connections.